The Untold Story of Trump's Failed Attempt to Overthrow Venezuela's President

On September 26, 2018, Venezuelan president Nicolás Maduro approached the lectern at the United Nations General Assembly in New York City. Hulking and mustachioed, wearing a black suit and a bright red tie, Maduro was in a bilious mood.

At home, Maduro’s political position was deteriorating. The former bus driver turned autocrat had ruled Venezuela for five years, and had recently “won” reelection in a contest widely considered to be fraudulent. But he was facing stiffer-than-expected pushback. Anti-government protests were wracking the oil-rich South American nation. Hyperinflation was obliterating its economy. More than a million Venezuelans had fled, triggering a hemispheric refugee crisis.

For some time, the Trump administration had been working furiously to push Maduro—an ally of Cuba and Russia—out of power. In fact, then-president Donald Trump had even mused publicly about exercising “a possible military option, if necessary,” to deal with Venezuela. The day before Maduro’s General Assembly address, Trump stood at the same UN podium, called the situation in Venezuela a “human tragedy,” and decried the “suffering, corruption, and decay” wrought by communist and socialist regimes. The US president then announced the imposition of new sanctions against members of Maduro’s inner circle.

When Maduro began his UN address, he was raring to punch back. His country was the “victim of a permanent aggression” by the “imperial” United States, he said. Venezuela’s attempt at geopolitical independence—and huge gold and petroleum reserves—had aroused the ire and avarice of the “oligarchies of the continent and those who dominate from Washington,” he added.

Maduro’s harangue got darker. He claimed that a recent attempt on his life—two drones had exploded during an address he was giving outdoors in Caracas—had been masterminded by shadowy actors from within the United States. (Trump administration officials publicly denied any role in the drone attack and a dissident member of the Venezuelan army later claimed responsibility.) In recent days, Maduro had even said he was considering skipping the UN meeting altogether, because he was worried about an assassination attempt.

As bitter adversaries, the Trump administration and Maduro regime didn’t agree on, well, anything. Except for the fact that the US government wanted Maduro gone.

After that UN meeting, the Trump administration amped up its efforts around the world to isolate and depose the Venezuelan leader, including by levying additional punishing sanctions against his regime. Much of that diplomatic maneuvering played out in public. But the administration also put into motion another, very much secret prong to the US’s regime-change campaign: a covert CIA-run initiative to help overthrow the Venezuelan strongman.

That campaign would pull off at least one disruptive digital sabotage operation against the Maduro regime in 2019. But the CIA-led initiative—alongside the Trump administration’s wider efforts to get rid of Maduro—would fall well short of its ultimate goal. The story of that secret anti-Maduro effort also lays bare the tensions between an administration with hardliners laser-focused on deposing the Venezuelan autocrat and a CIA deeply reluctant, yet nevertheless obligated, to follow White House orders. It shows the limitations of covert, CIA-assisted regime change schemes, particularly when they are not aligned with larger US foreign policy objectives. And it provides new insights into how a second Trump administration—or a Harris presidency—might still try to dislodge the Venezuelan strongman, whose latest sham reelection in July 2024 has again thrust his country into chaos.

The details of that covert CIA-assisted campaign, told exclusively to WIRED by eight Trump administration and former agency officials with knowledge of the anti-Maduro operation, are reported here for the first time.

On January 23, 2019, Venezuelan opposition leader Juan Guaidó stood before throngs of cheering protestors at a rally in Caracas. With his right hand held aloft, he declared himself interim president of Venezuela, with the full backing from the National Assembly, the country’s highest legislative body. That day, Guaidó vowed to “reestablish the constitution”—which many believed Maduro, whose second term had begun earlier that month, had repeatedly trampled.

Guaidó’s rise in 2019 helped cement US national security advisor John Bolton’s conviction that “it was time to turn the screws” on Maduro, according to Bolton’s memoir. “The revolution was on,” writes Bolton. After Guaidó’s speech, the administration recognized him as Venezuela’s rightful acting leader, and went to work lobbying other countries to do the same. (Around 60 countries would ultimately recognize Guaidó.) In late January, the Trump administration also announced its harshest Venezuela-related sanctions to date, targeting the country’s state-owned oil company and freezing billions of dollars in Venezuelan state assets. Around that time, the administration turned to the CIA to seek the agency’s help in ousting Maduro, according to former US officials familiar with the secret program. (Sources requested anonymity to discuss sensitive White House deliberations and CIA operations. The CIA declined to comment.)

The CIA quickly assembled a Venezuela Task Force. That group had its work cut out for it. Before the Trump administration’s directive, Venezuela was a low priority at Langley, and capabilities had to be built from the ground up, according to the administration and former CIA officials. One of the task force’s first goals: an expansion of efforts to hack Venezuelan government networks and other infrastructure targets for intelligence-gathering purposes.

Very quickly, the task force ran into roadblocks. It had to fight—sometimes unsuccessfully—for access to important resources, like elite CIA and NSA hacking teams. Those teams usually worked on higher-profile targets, according to a former agency official. In fact, when officials in the administration asked to have NSA hacking resources redirected to Venezuela, a former Trump-era official said top Pentagon officials “pushed back hard.”

Ultimately, the CIA successfully carried out a disruptive strike against Maduro: a cyberattack on the state-administered payroll system used to compensate members of Venezuela’s military, according to four Trump administration and former CIA officials. The gambit, which took months for the agency to even attempt thanks to the internal struggle for resources, had been designed to push teetering Venezuelan military officials to the Guaidó camp.

Former officials differ slightly in their descriptions of the payroll-related operation. Some characterize it as a remote-access cyberattack; others, as a digital sabotage operation enabled by agents on the ground. Regardless of how the cyberattack was carried out, the result was unhappy soldiers—and a risk to Maduro’s grip on power.

Temporarily denying Venezuelan soldiers from receiving their paychecks was part of the administration’s goal to “exacerbate, or just further reveal, the ineptitudes of the regime,” a former national security official says. And it had some effect, says a former senior official: “There was a fair amount of grumbling about not getting paid,” the official says. “Armies march on their stomach.”

The secret CIA-led campaign had other prongs too. The agency launched a covert influence campaign to spread pro-democracy content online in Venezuela, spun up a “democracy promotion” program to secretly sponsor leadership trainings, and provided support to Venezuelan civic groups, according to former US officials.

But as these efforts got under way, more cracks between the administration and the CIA started to show. Trump administration officials were unimpressed by the agency’s “democracy promotion” efforts. The CIA’s secret program appeared to be indistinguishable from pro-democracy initiatives carried out openly by other government agencies like USAID, according to four former officials. It was “the most embarrassing bullshit ever,” says a former national security official—“not even sinister,” but “purely lazy.” To some Trump administration officials, the presence in Venezuela of a viable, legitimate opposition leader like Guaidó, and the ongoing humanitarian catastrophe in the country, made the CIA’s covert “pro-democracy” campaign appear farcical.

“The average person has lost 25 pounds,” a former official says. “They have no food, they have no electricity, they have no jobs, they have no medicine. And we’re going to tell them about democracy?”

All this led some administration officials to believe that the CIA was focusing on the democracy-promotion efforts to wriggle out of conducting more hard-edged covert operations. It “was their excuse for not doing other things,” says a former US official. “I felt like they were playing with us.”

“The CIA is not the Mossad. It’s hunkered down, bureaucratic, and not daring … I’d like to see an intelligence community that’s more capable of carrying out clandestine operations in support of American policy,” Bolton tells WIRED. (Bolton declined to comment on any specific agency activities or discussions within the Trump administration about Venezuela-related covert operations.)

To some Trump-era officials, CIA executives—including CIA director Gina Haspel—were clearly opposed to the administration’s directive. Haspel “never bought into doing anything aggressive in Venezuela because she was still of the mind that we were ugly Americans,” says a senior Trump-era official. Haspel declined to comment.

“Part of the intelligence community is still traumatized by the Bay of Pigs invasion and failure. That’s number one,” Bolton says. “Number two, other parts of it are still traumatized by the Obama administration view that we have no enemies in Latin America. Castro regime’s OK. Chavez-Maduro regime’s OK. They’re not really threats. Ortega and Nicaragua was not really a threat. That wasn’t my view.”

Still, administration officials continued to push the CIA and Pentagon to take combative actions. Like one that involved Cuba.

Cuba relies on oil from Venezuela. In return, US officials believe, the Cuban security services have helped protect Maduro, essentially serving as an on-the-ground praetorian guard for the embattled socialist autocrat. The Trump administration thought if the US could somehow intercept or sabotage the oil ships sailing from Venezuela to Cuba, it could strike a blow against both regimes. Senior administration officials held meetings with paramilitary experts to look at the mechanics of such an operation. At least one option involved the CIA, which had a mobile system that could covertly (and nonviolently) disable ships. Trump administration officials wanted the agency to move the system near Venezuela, to hit some of its fuel tankers. The agency balked. CIA officials explained that it only had one of these systems, that it was currently in another hemisphere, and they didn’t want to move it to the northern end of South America. The idea was shelved.

That wasn’t the end of it. Some administration officials lobbied for US special operators to conduct sabotage operations within Venezuela. But US intelligence and Pentagon officials were deeply opposed to having any American boots on the ground in the country. Those options were taken off the table too.

At least once, Colombia stepped into the breach. The Colombians have a long history of working with CIA and Pentagon paramilitaries. Now they agreed to launch an operation inside Venezuela to disable some of the Venezuelan air force’s prized Russian-made Sukhoi fighter jets. The US provided targeting intelligence. But when the Colombian operatives carried out the sabotage, says a former senior official, the gambit was not as successful as initially hoped. The operatives were able to disable just a few of the aircraft.

As the days went by, hawks like Bolton tried to keep Trump focused on ousting Maduro. The national security advisor wrote in his memoir that, in a late January 2019 phone call with the opposition leader, Trump had assured Guaidó he’d “pull off Maduro’s overthrow.” On that call Trump had also, Bolton writes, alluded to the US’s interest in Venezuela’s oil. But as various efforts plodded along, the president’s confidence in Guaidó’s team started to waver.

Trump just wasn’t sure Guaidó was up for the job. In contrast to the “strong” Maduro, Trump thought Guaidó was “weak,” writes Bolton. The president began to refer to Guaidó as the “Beto O’Rourke of Venezuela.” In early March of that year, according to the memoir, Trump told Bolton, “He doesn’t have what it takes.”

Bolton and his allies didn’t let up. They even developed “day after” plans for Guaidó’s ascension. A pilot program spearheaded by the US Treasury Department, known as “Venezuela Day One,” was to involve the mass distribution of preloaded debit cards, from the Spanish banking powerhouse Banco Santander, which worked closely with the administration on the initiative. The idea was to give a financial lifeline to needy Venezuelans in the immediate post-Maduro era. That plan, along with other “day after” initiatives, ended up shelved. Banco Santander declined WIRED’s request to comment.

Illustration: Sam Green

Meanwhile, fractures within the administration deepened. Even by the hawkish standards of the Trump administration, the Bolton camp’s Venezuela strategy was considered aggressive. At one point, officials created a working group focused on Venezuela. It included the CIA and the State, Treasury, and Defense departments. One group it—intentionally—did not include: Bolton and his allies on the National Security Council, says a former State Department official. The CIA “sort of thought they were dealing with Oliver North,” another official says, adding that the spy agency “reacted in an equal and opposite direction” to what they felt was Bolton’s aggressiveness by trying to avoid any operations that could cause blowback for the CIA.

Schisms even opened between administration hawks. By March 2019, the security situation in Venezuela was spiraling ever-downward. Secretary of State Mike Pompeo decided to shut down the US embassy in Caracas that same month. Some administration officials believed Pompeo was primarily worried about the political fallout of presiding over “another Benghazi”—the 2012 attack by Islamist militants on US government facilities in Libya that killed four Americans, including the ambassador. “Pompeo made part of his career criticizing the Obama administration on the failures in Benghazi,” Bolton says. “And I do think that was kind of etched in his mind." Pompeo did not respond to requests for comment.

Yet other former officials emphasized the existence of specific, credible threats of violence by the Maduro regime to embassy personnel, including to the top US diplomat in the country. (“It definitely was not a sort of middle-of-the-night Pompeo panic,” says a former State Department official. “There were direct threats that had been made.”)

Whatever Pompeo’s motivations, the closure of the embassy would have major implications for US intelligence-gathering in Venezuela—and for the larger US-backed push to oust Maduro, say some former officials. It was a “disaster,” one former US official says.

The US still had ways to spy on Venezuelan targets remotely. But before the embassy closure, officials in Washington would talk to important Venezuelans, taking the political temperature and coordinating potential defections from the Maduro camp; then CIA and State Department officials on the ground in the country would confirm details with these people in person. By shutting down the embassy, say Trump-era officials, US efforts to oust Maduro were dealt a big blow. “It all got screwed up in the stupidest way,” a former national security official says.

Of course, much in Venezuela was outside the control of officials in Washington. The opposition was working with sympathetic regime members to lobby members of Venezuela’s high court to rule Maduro’s reelection illegitimate. It was also negotiating with powerful regime members, including Maduro’s own defense minister, to cut Maduro loose. But the opposition made some big missteps.

After a bunch of delays, Guaidó’s plan to overthrow Maduro was—finally—to come together on April 30, 2019. That day, Guaidó publicly announced “Operation Liberty,” exhorting military members to defect and calling for massive street protests. Trump administration officials believed that Maduro was close to abdicating the presidency, maybe even fleeing to Cuba.

Then it all fell apart.

There was a lot of miscommunication and mistrust between critical players in the opposition and Maduro’s equivocating supporters. At the last minute, major Venezuelan officials backed off the ledge. Mass military desertions failed to materialize. The Venezuelan high court chickened out. The protests were a flop. Maduro, bolstered by Cuban security forces at his side, rallied his supporters. The momentum had shifted against regime change. Though the Venezuelan opposition—and the Trump administration—would limp along in their attempts to oust Maduro, the best chance had been lost. Trump administration officials found themselves “spinning the[ir] wheels for months,” says a former national security official.

If the CIA had intervened more forcefully between January and April—when schisms within the military and among other Venezuelan elites were the biggest and Guaidó had the most momentum—it might have helped catalyze Maduro’s ouster, say former officials. But the agency didn’t.

“As [former secretary of defense Donald] Rumsfeld once said, you go to war with the army you have,” Bolton says. “And we had a lack of capability in a number of agencies, including the intelligence community. We couldn’t wait around for them to happen. So we had to do the best we could."

“There was a handful of sabotage and cyber stuff that was done,” says a former national security official. “But it was too little, too late.” Even the one major CIA action—the digital sabotage operation that disabled the Venezuelan military payroll system—happened after the opposition began to lose momentum in 2019, according to the former official.

After the payroll sabotage operation, the Venezuela Task Force began to wither. “It was kind of a one trick pony,” says a former senior agency official. CIA officials were “doing this 16 hours a day for four weeks. And then it’s over—nobody gives a shit anymore,” says another former agency official. This sort of frenzied, time-compressed approach to covert action was highly unusual, this person adds.

“Trump never made it enough of a priority for the rest of the national security components of the government to step up” and help overthrow the Venezuelan leader, says a former senior administration official. “Haspel,” the source says, “was absolutely not inclined to lean forward unless someone brought her into the Oval Office and said, ‘You know, you have to do this.’ And it never reached that point.” What’s more, in September 2019, Trump pushed out Bolton, the most steadfast driver of the administration’s Venezuela-related efforts.

When the presidency changed hands, the Biden administration tried a different approach. In October 2023, worried about rising gasoline prices and a spiraling refugee crisis—and looking to cleave Venezuela from Russia, China, and Iran’s orbit— administration officials brokered a deal with Maduro. For agreeing to allow free and fair presidential elections in July 2024 and accepting Venezuelan refugees deported by the US, the US would ease some of the tough Trump-era sanctions on the nation’s energy sector.

Maduro quickly reneged on the deal. His administration disqualified and barred leading opposition candidates from running for president, and kicked off a broad anti-democratic crackdown. Six months later, the Biden administration reimposed oil sanctions against the regime.

This past July, Maduro declared victory in a vote once again marred by widespread fraud. Mass protests spread throughout Venezuela. Thousands of civilians were arrested. In August, US secretary of state Antony Blinken said there was “overwhelming evidence” that opposition candidate Edmundo González Urrutia had won the election. In September, fearing arrest or assassination, González fled to Spain. (In a recent interview, Trump called Maduro a “dictator,” but also seemed to praise the regime for what it claimed to be successful efforts to lower crime in Caracas, calling it “safer than many of our cities.”)

At the moment, the authoritarian Maduro’s grip on power seems secure. But there might be a “silver lining” to all the Venezuela-focused intelligence activity prompted by the Trump administration’s anti-Maduro campaign, a former CIA official says. Before that, US spy agencies had never devoted much energy to sophisticated cyberespionage or signals intelligence collection targeting Venezuela, according to the former official.

But now, this source says, US intelligence agencies have “a lot better access” to Venezuela-related intelligence. “There could be some benefit down the line.”

Image Source: Getty Images